Jermaine Dupri & Janet Jackson

Janet Jackson is one of the biggest names in Hollywood. She and her brother, Michael Jackson are among the royals in the music industry. Not only did she make a solid investment in her career, but she also spent some of her time, effort, and love on former boyfriend Jermaine Dupri. Unfortunately, after spending 7 years together, the two both decided to call it quits.

Jackson and Dupri remain to be one of the most intriguing couples of all time. Even though their relationship ended way back in 2008, both of them still seemed to open up about their previous love story from time to time. The beautiful singer recalled when she first met the producer, which was backstage in one of her concerts. She immediately thought he was cool, and unsurprisingly, so did he. Their chemistry took off not long after that as Dupri said he shall see Jackson again. She also gave a recap on an interview about how they called it quits.